Skyward Shift: Tyler Flagg’s Journey from Air Force Pilot to Aviation Entrepreneur

By Viktoria Capek

Tyler Flagg, a former Air Force pilot, is reshaping the story of corporate aviation through his pioneering startup, Flying Company. Fueled by a mix of military discipline, entrepreneurial zeal, and a profound love for flying, he is revolutionizing the aviation landscape.

Flagg’s story is one of evolution, transitioning from a child actor in Jersey City to a distinguished Air Force pilot who has circled the globe, touching down in 67 countries.

A defining moment during pilot training, where he landed on a pitch-black dirt strip using night vision goggles, set the stage for a career that would be anything but ordinary. Reflecting on those early days, Flagg confessed he was a young co-pilot with a single thought: “Man, this is really cool.”

In 2021, after a decade of serving in the Air Force, Flagg took an unexpected turn. An internship in Los Angeles at a tech startup through the DOD Skillbridge program revealed a new opportunity in Bentonville, Arkansas. A friend’s suggestion led him to explore chief pilot opportunities.

“Corporate aviation is a whole lot more personal and high touch than the airlines,” Flagg recalled, a memory that led him to his career decision to move to Arkansas.

This venture, founded on keen observations of the corporate aviation landscape, eventually became Flying Company. The platform connects operators with contract pilots, addressing industry pain points Flagg witnessed firsthand during his time in the skies.

“I saw what corporate aviation was lacking,” Flagg said.

As Flagg delved into entrepreneurship, The Venture Center’s Veteran Owned Small Business Accelerator program became a crucial ally. This one-man band found solace and guidance within the community.

“It’s really nice to be able to bounce questions off of people,” Flagg said about the VOSBA organizers and other cohort members. “They’ve been excellent in terms of giving me advice and pointing me in the right direction.”

Flagg’s journey encompasses not just a career shift but a paradigm shift—from the vast skies to the dynamic world of corporate aviation. This precision extends beyond the cockpit; it weaves into his philosophy of involving his children in the entrepreneurial journey.

“I try to involve them as much as possible because I would love for my kids to kind of take on the entrepreneurial spirit and build something themselves,” Flagg said. “Even if it doesn’t work out for me, hopefully, they can learn from my mistakes or whatever and do better when they grow up.”

As Flagg ventures into entrepreneurship, he not only paves a path for success but also encourages the next generation to embrace entrepreneurial passion.

Learn more about Tyler Flagg and Flying Company, here.